Amine alkoxy chalcone compound and preparation method and application thereof

A technology of amine alkoxy chalcone and compound, which is applied in the field of amine alkoxy chalcone compound and preparation thereof, can solve the problem of ineffective prevention, poor butyrylcholinesterase inhibitory activity, poor therapeutic effect, etc. problem, to achieve the effect of strong antioxidant activity

Active Publication Date: 2019-09-17
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In previous reports, scutellarin aglycon carbamate derivatives (CN10337956A, CN102603698A), stilbene or ethane carbamate compounds (CN102816090A), and isoflavone carbamate compounds (CN102827131A) were discovered. Ferulic acid carbamate compounds (CN105837497A, CA105601540A, CN105646289A), although these compounds have better acetylcholinesterase inhibitory activity and antioxidant activity, and have a little inhibitory effect to Aβ aggregation, simultaneously to butyrylcholinesterase Enzyme inhibitory activity is very poor, r

Method used

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  • Amine alkoxy chalcone compound and preparation method and application thereof
  • Amine alkoxy chalcone compound and preparation method and application thereof
  • Amine alkoxy chalcone compound and preparation method and application thereof

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Embodiment 1

[0045] A kind of amine alkoxy chalcone compound, its general chemical structure formula is as shown in (I):

[0046]

[0047] Among them, n, R 1 , R 2 See Table 1 below for definitions.

[0048] Table 1 Amine alkoxy chalcone compound of the present invention

[0049]

[0050]

[0051]

[0052]

[0053] A preparation method of amine alkoxychalcone compound, comprising the following steps:

[0054] (1) Add 2.0mmol of the corresponding 3-hydroxybenzaldehyde (1), 3.0mmol of potassium carbonate, 6.0mmol of dibromide (2) and 15mL of acetonitrile into the reaction flask, heat to 65°C for 10 hours, and after the reaction, After conventional treatment, it was purified by silica gel column chromatography (eluent: petroleum ether: acetone = 50:1v / v) to obtain the corresponding alkoxybenzaldehyde (3);

[0055] (2) corresponding alkoxybenzaldehyde (3) 2.0mmol, secondary amine NR 1 R 2 (4) 2.5mmol and 3.0mmol potassium carbonate were added to a reaction flask containing...

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Abstract

The invention discloses an amine alkoxy chalcone compound, and a preparation method and application thereof. The preparation method comprises the following steps: (1) 3-hydroxybenzaldehyde is used as a starting material and reacts with a dibromide compound under a first solvent and a first alkaline condition to obtain bromoalkoxybenzaldehyde; (2) the bromoalkoxybenzaldehyde reacts with secondary amine in a second solvent under a second alkaline condition to obtain amine alkoxy benzaldehyde; and (3) the amine alkoxy benzaldehyde and 2-hydroxyacetophenone are subjected to a third solvent and a third alkaline condition to obtain the target compound, i.e. amine alkoxy chalcone compound. The amine alkoxy chalcone compound has selective butyrylcholinesterase inhibitory activity, selective monoamine oxidase B inhibitory activity, selective metal ion chelating activity and Abeta aggregation inhibitory activity in vitro, and can be used for treating and/or preventing neurodegenerative related diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to an amine alkoxychalcone compound, a preparation method and application thereof. Background technique [0002] Alzheimer's disease (AD) is one of the diseases with the highest morbidity and mortality among the elderly. According to the "2015 Global Alzheimer's Report" released by Alzheimer's Disease International (ADI), more than 46 million people in the world suffered from dementia in 2015. It is predicted that by 2050, the world's There will be 131.5 million people suffering from dementia, and the incidence rate of dementia patients in China has reached 6.61%. With the prolongation of the average life expectancy, the disease has developed into a major burden on the society and the medical care system, and has brought heavy mental and economic pressure to the society, patients and their families. The drugs currently approved by the FDA are mainly acetylcholinesterase inhibito...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C217/22C07C217/58C07D219/10C07D295/088C07D295/096C07D211/14C07D217/04C07D491/107A61P25/28A61P25/16A61P25/14A61P25/04A61P25/00A61P27/06
CPCC07C217/22C07C217/58C07D219/10C07D295/088C07D295/096C07D211/14C07D217/04C07D491/107A61P25/28A61P25/16A61P25/14A61P25/04A61P25/00A61P27/06
Inventor 桑志培王柯人柳文敏于林涛时健程新峰杨丹张子怡
Owner NANYANG NORMAL UNIV
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